Diethylene Glycol → 2-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanol

HRID 651504

Reaction equation

HRID 651504 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[Cl-].[CH3:11][SiH:12]([CH3:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[CH3:14][C:13]([Si:12]([CH3:17])([CH3:11])[O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 24758Sodium hydrideHCID 131722836Tert-butyldimethylsilane chloride

Product 1

HCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanolYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 g of diethyleneglycol is added to 9.05 g of sodium hydride in 320 cm3 of tetrahydrofuran, the reaction medium is agitated for 45 minutes, 28.3 g of dimethylterbutylsilane chloride is added, agitation is carried out for 3 hours while leaving the temperature to return to ambient. Extraction is carried out with ether, followed by washing with an aqueous solution of sodium bicarbonate, with salt water, drying and evaporating the solvent. 40.25 g of expected product is obtained.

Workup

  1. waitagitation is carried out for 3 hours
  2. customwhile leaving the temperature
  3. extractionExtraction
  4. washby washing with an aqueous solution of sodium bicarbonate, with salt water
  5. customdrying
  6. customevaporating the solvent

Sources & evidence

ORD record
ord-ea06e4a76b824325b25c383d0b6d803b
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Linked notes

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